Chemical synthesis of archaeosine

Archaeosine is a hypermodified nucleoside found in archaeal tRNAs, and their biosynthesis and functions have been sudied for a long time. The supply of pure archaeosine by chemical synthesis is important for promoting such research, but existing methods have some shortcomings, such as low synthetic yields. We have developed an efficient method for the synthesis of archaeosine using PreQ₀-nucleoside as an intermediate. In addition, we applied this method to the synthesis of PreQ₀-nucleoside-lysine adduct 1. Collaborative research with Prof. Yokogawa of our Department has revealed that 1 is a biosynthetic intermediate of archaeosine.

1) Oka, N.; Fukuta, A.; Ando, K. Tetrahedron 2018, 74, 5709-5714.

2) Yokogawa, T.; Nomura, Y.; Yasuda, A.; Ogino, H.; Hiura, K.; Nakada, S.; Oka, N.; Ando, K.; Kawamura, T.; Hirata, A.; Hori, H.; Ohno, S. Nat. Chem. Biol. 2019, 15, 1148-1155.